Yellow substantive azo dyestuffs and process of making the same



United States Patent $1. 2? 323 and kept at this temperature for48"-T60 hours.. When. :1 2,787,614 sample shows no longer a change of color with sodium YELLOW SUBST E AZO DYESTUFFS AND carbonate solution, the alcohol is blown o'fl. with steam,

and the dyestutf is filtered off and dried. PROCESS OF MAKING THE SAME The dyestutf obtained excels Chrysophenine G (cf. G.

Eugen Huber, Ottmar Wahl, and Josef Hilger, Lever- 5 Schultz Farbstofftabellen, 7th edition, No. 726) by a kuseu-Bayerwerk, Germany assignors to Farbendistinctly improved fastness to wet-treatment. The dyefabi'ikeii Bayer Aktieng'esells'chaft', Leverkusen, Gerstuff corresponds as free acid to the formula many, a corporation of Germany S0 H No Drawing. Application September 21, 1954, 1 I I senal ci.om.om.o.ens.cn .o- N=N--CH Claims'pi'iority, application Germany October 1, 1953 p 7 n 6Claims. (Chim -178) cromomocmcmm- N==N-C CH The present invention relates to new yellow substantive 0,11

azo dyestuffs and t'o'a process of making tlie same; more M particularly it relates to azo dyestutfs of the type The alkylation can, if desired, also be carried out in Yellow substantive azo dyestuffs of this type are known 1 aqueous solution without pressure. Instead of fi,,9'-die. g. from German Patent 42,466. Dyestulfs of this kind chloro-diethyl ether also the homologs of it may be are known as Chrysophenine. They are obtained by employed. coupling tetrazotized 4,4'-di-aminostilbene-2,2'-disulfonic acid with 2 mols of phenols and subsequent etherifying Example 2 of these disazo dyestulfs to make them fast to alkalides. If in Example 1} B fl' di h1 di thyl ether is replaced In this known process alkyl halides and salts of alkyl b 260 y parts by weight of formaldehyde bis (5 chlord fu a s are mentloned as alkylat'mg agents ethyl)-acetal, a dyestuff is obtained which also'shows a According to the present invention azo dyestulfs of this type, however, of improved properties are obtained by using instead of the hitherto used alkylating agents dihalogeno ethers or acetals in which the halogen atoms 5093 do not stand in neighbouring position to the ether oxygen.

Such alkylating agents are e. g. 2,2'-dichloro diethyl ether, 'O C 4,4'-dichloro dibutyl ether formaldehyde-bis-(fl-ehlorodistinctly improved fastness to wet-treatment. It corresponds as free acid to the formula:

ethyl)-acetal [Cl.CHaCHz.O.CH2.O.CH2.CH2.C1] or the O OH OH OCH CH CH G corresponding acetaldehyde acetal. The new yellow sub- 40 stantive azo dyestufis obtained by using these alkylating agents excel the dyestuflfs known e. g. from German Patent 42,466 by greater brilliance of the shade particu- We claim:

larly, however, by better fastness to wet treatment. 1. In the process of making yellow substantive azo dye- The new dyestuffs correspond to the general formula: stuffs by alkylating disazo dyestuffs obtained from tetrazowherein X stands for hydrogen or CH3, m means integer tized 4,4'-diamin0stilbene-2,2'-disulfonic acid and 2 mols of at least 2, and n one of the figures 0 and 1. 0f monohydroxy benzene the step which consists in al- The following examples illustrate the present invenkylating with dichloro compounds selected from the tion without, however, limiting it thereto; the parts by 30 group consisting of dichloro ethers and acetals thechlo weight and the parts by volume stand in the ratio of time atoms of which are in a position other than alpha to gramme to cubic centimetre. the ether oxygen atom. 1

Example 1 2. In the process of making yellow substantive azo dyestuffs by alkylating disazo dyestufls obtained from 364 parts by weight of Brilliant Yellow (cf. G. Schultz tetrazotized 4,4'-diaminostilbene-2,2'-disulf0nic acid and Farbstofitabellen, 7th edition, No. 724) as a moist 2 mols of monohydroxy benzene the step which consists about 60 percent paste are well mixed with 660 parts by in alkylating with 2,2'dichloro diethyl ether. volume of alcohol and 60 parts by weight of water in 3. In the process of making yellow substantive azo an autoclave. After adding 150 parts by weight of a 33 dyestuffs by alkylating disazo dyestuffs obtained from percent caustic soda solution, parts by weight of 70 tetrazotized 4,4'-diaminostilbcne-2,2-disulfonic acid and2 sodium carbonate and 210 parts by weight of p3,[3'-dimols of monohydroxy benzene the step which consists in chloro-diethyl ether, the mixture is heated to -97 C. alkylating with Cl.CH2.CHa.O.CH2.O.CH2.CH2.C1.

as free acid to the formula: i l I v I M O1.CH2.CHLQOHLQQHLDH Df I N=N CH 1i m sayrsmem I a I 6. The yellow substantive azo dyestuff corresponding wherein X stands for a radical selected from the group asfree acid to the formula:

consisting of hydrogen and methyl, m means an integer 5 at least 2 4] 9 "F fi f 9 Cl.CH2.CHzD.OH|.O.OH2.CH2.OON=N 5. The yellow substant ve ,azo dyestuff corresponding l References Cited in the file of this patent o1.omom.0.oi1,.cm.o-C N=N UNITED STATES PATENTS 1,975,830 Dahlen Oct. 9, 1934 FOREIGN PATENTS 3,994 Great Britain of 1887 O I 2,568,579 Coleman Sept. 18, 1951 Cl.CHs.CH1-O.CHs.CH|.O N=N on a 

1. IN THE PROCESS OF MAKING YELLOW SUBSTANTIVE AZO DYESTUFFY B ALKYLATING DIAZO DYESTUFFS OBTAINED FROM TETRAZOTIZED 4,4''-DIAMINOSTILBENE-2,2''-DISULFONIC ACID AND 2 MOLS OF MONOHYDROXY BENZENE THE STEP WHICH CONSISTS IN ALKYLATING WITH DICHLORO COMPOUNDS SELECTED FROM THE GROUP CONSISTING OF DICHLORO ESTERS AND ACETALS THE CHLORINE ATOMS OF WHICH ARE IN A POSITION OTHER THAN ALPHA TO THE ETHER OXYGEN ATOM. 